27548-93-2

Basic information

• Product Name: Baccatine III
• Synonyms: BACCATINE III;BACCATIN III;baccatin Ⅲ;BACCATIN III 98%;(1S)-4α,10β-Bis(acetoxy)-2α-(benzoyloxy)-5β,20-epoxy-1,7β,13α-trihydroxytaxa-11-ene-9-one;(2aR)-6α,12bβ-Bisacetoxy-12β-(benzoyloxy)-1,2aβ,3,4,4a,6,9,10,11,12,12aβ,12b-dodecahydro-4α,9β,11β-trihydroxy-4aα,8,13,13-tetramethyl-7,11-methano-5H-cyclodeca[3,4]benzo[1,2-b]oxete-5-one;(2aR)-6α,12bβ-Diacetoxy-12β-benzoyloxy-1,2aβ,3,4,4a,6,9,10,11,12,12aβ,12b-dodecahydro-4α,9β,11β-trihydroxy-4aα,8,13,13-tetramethyl-7,11α-methano-5H-cyclodeca[3,4]benzo[1,2-b]oxete-5-one;6α,12bβ-Diacetoxy-12β-benzoyloxy-1,2aβ,3,4,4a,6,9,10,11,12,12aβ,12b-dodecahydro-4α,9β,11β-trihydroxy-4aα,8,13,13-tetramethyl-7,11α-methano-5H-cyclodeca[3,4]benzo[1,2-b]oxete-5-one
• CAS NO: 27548-93-2
• Molecular Formula: C₃₁H₃₈O₁₁
• Molecular Weight: 586.63
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics;Chiral Reagents;Heterocycles;Inhibitors
• Mol File: 27548-93-2.mol
• Article Data: 56

Chemical Properties

• Melting Point: 229-234 °C
• Boiling Point: 562.81°C (rough estimate)
• Flash Point: 226.9 °C
• Appearance: White to off-white/Solid
• Density: 1.2062 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5455-1.5475
• Storage Temp.: 2-8°C
• PKA: 12.76±0.70(Predicted)
• Water Solubility: insoluble
• Stability: 4 Year Shelf Life
• CAS DataBase Reference: Baccatine III(CAS DataBase Reference)
• NIST Chemistry Reference: Baccatine III(27548-93-2)
• EPA Substance Registry System: Baccatine III(27548-93-2)

Safety Data

• Hazard Codes: T
• Statements: 45-46-22-36/37/38-48/20/22
• Safety Statements: 53-22-26-36/37/39-45-24/25
• RIDADR: 1544
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 27548-93-2(Hazardous Substances Data)

Usage

Chemical Properties

White to Off-White Powder

Uses

Different sources of media describe the Uses of 27548-93-2 differently. You can refer to the following data:
1. A precursor to Paclitaxel, a neoplasm inhibitor to ovarian and breast cancers found in Taxus species
2. immunomodulator, induces apoptosis
3. Precursor to paclitaxel

Definition

ChEBI: A tetracyclic diterpenoid isolated from plant species of the genus Taxus.

InChI:InChI=1/C31H38O11/c1-15-19(34)13-31(38)26(41-27(37)18-10-8-7-9-11-18)24-29(6,20(35)12-21-30(24,14-39-21)42-17(3)33)25(36)23(40-16(2)32)22(15)28(31,4)5/h7-11,19-21,23-24,26,34-35,38H,12-14H2,1-6H3/t19-,20-,21+,23+,24+,26-,29+,30-,31+/m0/s1

Upstream product

• 33069-62-4 taxol 
• 115437-21-3 7-(triethylsilyl)baccatin III 
• 32981-86-5 10-deacetylbaccatin III 
• 591-51-5 phenyllithium 
• 187961-12-2 C₂₈H₃₃Cl₃O₁₃ 
• 187961-14-4 C₃₅H₅₁Cl₃O₁₂Si 
• 187960-89-0 (1S,5S,6S,7S,8S,12S)-6-((R)-2-Benzyloxymethoxy-1-methylene-pent-4-enyl)-7,11,14,14-tetramethyl-8-triethylsilanyloxy-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.0^1,5]tetradec-10-ene-3,9-dione 
• 187960-99-2 C₃₅H₅₂BrCl₃O₁₂Si 
• 187961-01-9 C₃₇H₅₃Cl₃O₁₃Si 
• 187961-10-0 Benzoic acid (1S,2S,3R,4S,5S,7S,8S,10R,13S)-10-acetoxy-5-bromo-1,2,4-trihydroxy-8,12,15,15-tetramethyl-9-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-13-triisopropylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadec-11-en-4-ylmethyl ester 
• 187961-11-1 C₄₂H₅₆BrCl₃O₁₃Si 
• 75-36-5 acetyl chloride 
• 72-89-9 acetylcoenzyme A 
• 189006-03-9 10-deacetylbaccatin III 

Downstream Products

• 103150-33-0 7-(2,2,2-trichloroethyloxycarbonyl)baccatin III 
• 32981-89-8 13-oxobaccatin III 
• 204579-93-1 C₄₄H₄₈O₁₂ 
• 265659-42-5 7-(1,2-O-isopropylidene-malyl) baccatin III 
• 32981-86-5 10-deacetylbaccatin III 
• 71629-92-0 10-deacetyl-7-epi-baccatin III 
• 31077-81-3 7-epi-baccatine III 
• 1315376-87-4 C₅₃H₅₈⁽²⁾H₅NO₁₃Si 
• 1315376-88-5 C₅₃H₆₀⁽²⁾H₅NO₁₅Si 
• 1315376-89-6 C₅₃H₆₀⁽²⁾H₅NO₁₅Si 
• 1315376-90-9 C₄₇H₄₆⁽²⁾H₅NO₁₅ 
• 1129540-33-5 C₄₇H₄₆⁽²⁾H₅NO₁₄ 
• 1315376-85-2 C₅₃H₆₀⁽²⁾H₅NO₁₄Si 
• 1315376-86-3 C₅₄H₅₉⁽²⁾H₅F₃NO₁₆SSi 

Relevant articles and documents

Synthesis, utility, and x-ray crystal structure of novel complexes of baccatin III with imidazole and 2-propanol

(matrix presented) Baccatin III forms crystalline complexes 4 and 5 with imidazole and 2-propanol, respectively. These compounds are useful in the purification of baccatin III from mixtures of taxanes derived from plant-cell fermentation.

Selective protection of the C(7) and C(10) hydroxyl groups in 10- deacetyl baccatin III

New protocols for the selective protection of the C(7) and C(10) hydroxyl groups of 10-deacetyl baccatin III are described, leading to more efficient semisyntheses of taxol and taxol analogs. The C(10) hydroxyl group of 10-DAB can be highly selectively acylated or silylated, and subsequent selective protection of the C(7) hydroxyl group then becomes straightforward.

Fluorinated taxane compound, preparation method therefor and application of fluorinated taxane compound

The invention discloses a fluorinated taxane compound, a preparation method therefor and an application of the fluorinated taxane compound. The compound has a structural general formula represented bya formula I. Proven by pharmacological experiments, compared with paclitaxel, a series of fluorinated taxane derivatives synthesized by the method have cytotoxicity superior to that of the paclitaxelto a multidrug-resistant human mammary cancer cell line MCF-7/Adr and an ovarian cancer cell line NCI/Adr and represent cytotoxicity superior to that of the paclitaxel to a colon cancer cell line HCT-116 with overexpressed neoplasm stem cells.

Antagonizing NOD2 Signaling with Conjugates of Paclitaxel and Muramyl Dipeptide Derivatives Sensitizes Paclitaxel Therapy and Significantly Prevents Tumor Metastasis

A noncleavable paclitaxel (PTX) and N-acetylmuramyl-l-alanyl-d-isoglutamine (MDP) derivative conjugate, 22 (DY-16-43), and its analogues were prepared and characterized as antagonists of NOD2 signaling. This conjugate enhanced the antitumor and antimetastatic efficacy of PTX in Lewis lung carcinoma (LLC) tumor-bearing mice. This work first describes a molecular strategy that enables the sensitization of a chemotherapeutic response via antagonizing NOD2 inflammatory signaling and suggests NOD2 antagonist as potential adjunct in treating non-small-cell lung cancer (NSCLC).